Methanol → 4-(4-Hydroxyphenyl)butanoic acid methyl ester
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.O.[CH3:20]O>>[CH3:20][O:12][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1Participants
5
Procedure
The 4-(4-hydroxyphenyl)butanoic acid (1) (4.6 g) from the previous step was dissolved in methanol (60 mL), concentrated sulfuric acid (1 mL) was added, and refluxed by heating for two days. The reaction solution was poured into water, and extracted with ethyl acetate (200 mL). The organic layer was washed with water (50 mL), saturated aqueous solution of sodium hydrogen carbonate (50 mL) and saturated sodium chloride solution (50 mL). After drying on anhydrous sodium sulfate, filtration and vacuum concentration, the above-identified compound (4.9 g, yield 99%) was obtained.
Workup
- temperaturerefluxed
- temperatureby heating for two days
- extractionextracted with ethyl acetate (200 mL)
- washThe organic layer was washed with water (50 mL), saturated aqueous solution of sodium hydrogen carbonate (50 mL) and saturated sodium chloride solution (50 mL)
- dry with materialAfter drying on anhydrous sodium sulfate, filtration and vacuum concentration
Sources & evidence
- ORD record
- ord-ddabfb4001e74cad8d406a525cc3f8be
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318781B2
Reaction notes
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